Reese Witherspoon’s Top 3 Best and Worst Red Carpet Outfits

While Reese Witherspoon’s red carpet ensembles typically exude a southern polish, her outfit for the “Cruel Intentions” premiere was messy and disjointed. For the 1999 event, the star wore a beige blouse featuring a square, slightly jagged neckline and a gold ribbon wrapped and tied around the torso. The blouse was paired with a wrinkly midi skirt made of purple nylon and dark gray sandals, with Witherspoon opting for minimal makeup and wearing her hair in a wavy, half-up style. Overall, the look feels incohesive and informal enough to land on the worst outfit list, but it’s also disappointing premiere attire for what has endured as such a classic ’90s film.

Reese Witherspoon’s black gown for the 2002 Academy Awards definitely ranks as one of her all-time best red carpet looks, with the Hollywood figure wearing Valentino for her first ever appearance at the star-studded event. The sable dress featured a lace-trimmed, scalloped neckline and lacy sleeves paired with 1920s-reminiscent beading along the lower bodice and skirt. The “Legally Blonde” actor styled the glamorous piece with strappy heels, diamond-shaped earrings, and a slightly wavy bob. With Witherspoon being the queen of the little black dress, it’s not surprising that the actor dazzled us with this inky gown. 

On the flip side, Reese Witherspoon’s outfit for the 2009 Academy Awards ceremony was a major miss. She wore a floor-length gown from Rodarte to the event, with the garment boasting sparkly bodice embellishments, asymmetrical straps, and an a-line skirt in a cobalt blue-and-black color scheme. The “Walk the Line” actor styled the piece with smokey eyeshadow and black nail polish, wearing her blonde tresses in a half-up hairstyle. We blame this sartorial misstep on the gown, with its color-blocked skirt and uneven straps coming together for a wonky and haphazard look that even Witherspoon’s natural beauty couldn’t save.

Next, Reese Witherspoon also dazzled with the Christian Dior gown she wore to the 2006 Oscars. The champagne piece consisted of a combination sparkly embellishments and embroidered flowers that created a romantic, whimsical vibe. The book club founder, who’s had some great Reese’s Book Club selections for the 2020s, reminisced on the look via social media, mentioning it in response to a fan question posted to X. “I have fallen in love with so many costumes over the years and I keep one from every movie. But one special dress stands out!” she wrote. “My Oscar dress in 2006: it was a 1957 Christian Dior bought at a vintage store in Paris. So dreamy!” We completely agree, with the Oscar ensemble ranking as one of Witherspoon’s best.

Unfortunately, we weren’t big fans of the dress that Reese Witherspoon wore to the Glamour Women of the Year Awards in 2015. The star sported a long-sleeved piece from Erdem Resort, with the knee-length dress consisting of a blue, white, and black lace paired with all-black openwork at the high-neck collar. Witherspoon accessorized with black heels, sparkly earrings, and an assortment of rings, wearing her straightened hair down around her shoulders. While we feel the southern influence in this outfit, the multi-colored lace combined with the busy collar makes it visually overwhelming. It’s not a common complaint we have for Witherspoon, but we wish this piece was a little pared back.

Another one of our favorite Reese Witherspoon looks comes from the 2024 Screen Actors Guild Awards, as the “Daisy Jones & the Six” producer stunned in a bright red dress. The strapless Elie Saab piece featured a scoop neckline, structured draping, and V-shaped slit. The star paired the sizzling dress with matching, sandal-style heels from Aquazzura and a simple gold necklace, styling her hair with effortless waves and opting for a brown-toned eyeshadow. “It’s giving Pookie looks fire,” Witherspoon told E! News, lightheartedly referencing a TikTok meme. “It’s giving, you know, red! Lady in red!” We can’t deny that Witherspoon does look pretty fire in this sizzling red gown.